Research Article
BibTex RIS Cite

The catalytic activity of Palladium(II) complexes containing PN ligands in the Heck and Suzuki C-C coupling reactions

Year 2018, Volume: 5 Issue: 1, 133 - 148, 01.09.2017
https://doi.org/10.18596/jotcsa.341530

Abstract

A range of iminophosphine (PN) ligands ((C6H5)2P-C6H4-CH=NR
(R=-C6H3(2-CH3)(4-OH) (1a), -CH2CH2C6H4(4-OH)
(1b) and -C5H3N(2-CH3)
(1c))  have been synthesized starting from 4-amino-3-methylphenol,
4-(2-aminoethyl)phenol and 2-amino-3-methylpyridine with 2-(diphenylphosphino)benzaldehyde.
The PN ligands were reacted with Pd(cod)Cl2 to give corresponding new
PdLCl2 metal complexes, (2a,
2b and 2c).
The Heck and Suzuki C-C coupling reactions were examined with
catalysts 2a-2c and showed high conversions under the determined conditions with
para substituted arylhalides

References

  • 1. Aydemir, M., Baysal, A., Gümgüm, B., Synthesis and characterization of tris{2-(N,N-bis(diphenylphosphino) aminoethyl} amine derivatives: Application of a palladium(II) complex as a pre-catalyst in the Heck and Suzuki cross-coupling reactions. J. Organomet. Chem. 2008; 693: 3810-3814.
  • 2. Scrivanti, A., Beghetto, V., Matteoli, U., Antonaroli, S., Marini, A., Crociani, B., Catalytic activity of η2-(olefin)palladium(0) complexes with iminophosphine ligands in the Suzuki–Miyaura reaction. Role of the olefin in the catalyst stabilization. Tetrahedron 2005; 61: 9752-9758.
  • 3. Nadri, S., Joshaghani, M., Rafiee, E., Biphenyl-based phosphine: A well-defined, air-stable, and efficient ligand for the Mizoroki–Heck reaction. Applied Catal. A, 2009; 362: 163-168.
  • 4. Iranpoor, N., Firouzabadi, H., Motevalli, S., Talebi, M., Palladium nanoparticles supported on silicadiphenyl phosphinite (SDPP) as efficient catalyst for Mizoroki–Heck and Suzuki–Miyaura coupling reactions. J. Organomet. Chem. 2012; 708: 118-124.
  • 5. Iyer, S., Kulkarni, G.M., Ramesh, C., Mizoroki–Heck reaction, catalysis by nitrogen ligand Pd complexes and activation of aryl bromides. Tetrahedron, 2004; 60: 2163-2172.
  • 6. Gruber, A. S., Zim, D., Ebeling, G., Monteiro, A.L., Dupont, J., Sulfur-Containing Palladacycles as Catalyst Precursors for the Heck Reaction. Org. Lett. 2000; 2: 1287-1290.
  • 7. Doherty, S., Knight, J.G., Tom, H., Scanlan, T. H., Elsegood, M. R. J., Clegg,W., Iminophosphines: synthesis, formation of 2,3-dihydro-1H-benzo[1,3]azaphosphol-3-ium salts and N-(pyridin-2-yl)-2-diphenylphosphinoylaniline, coordination chemistry and applications in platinum group catalyzed Suzuki coupling reactions and hydrosilylations. J. Organomet. Chem. 2002; 650: 231-248.
  • 8. Cheng, J., Wang, F., Xu, J. H., Pan, Y., Zhang, Z., Palladium-catalyzed Suzuki–Miyaura reaction using aminophosphine as ligand. Tetrahedron Lett. 2003; 44: 7095-7098.
  • 9. Drew, D., Doyle, J. R., Cyclic diolefin complexes of platinum and palladium. Inorg. Synth. 1990; 28: 346-347.
  • 10. Laue, S., Greiner, L., Wöltinger, J., Liese, A., Continuous Application of Chemzymes in a Membrane Reactor: Asymmetric Transfer Hydrogenation of Acetophenone. Advan. Synt.& Catal. 2001; 343: 711-720.
  • 11. Keleş, M., Şahinoğlu, C., Emir, D. M., Mart, M., New iminophosphine–Ru(II) complexes and their application in hydrogenationand transfer hydrogenation. Appl. Organometal. Chem. 2014; 28: 768-772.
  • 12. Monteiro, A .L., Nobre, S. M., Pd complexes of iminophosphine ligands: A homogeneous molecular catalyst for Suzuki–Miyaura cross-coupling reactions under mild conditions. J. Mol. Catal. A 2009; 313: 65-73.
  • 13. Jeffrey, J.C., Rauchfuss, T. B., Tucker, P.A., Metal Complexes of Diiminodiphosphines. Structural and Reactivity Patterns. Inorg. Chem. 1980; 19: 3306-3315.
  • 14. Rulke, R. E., Kaasjager, V. E., Wehman, P., Elsevir, C. J., Leeuwen, P. W., Vrieze, K., Stable Palladium(0), Palladium(II), and Platinum(II) Complexes Containing a New, Multifunctional and Hemilabile Phosphino−Imino−Pyridyl Ligand:  Synthesis, Characterization, and Reactivity.Organomet. 1996; 15: 3022-3031.
  • 15. Crochet, P., Gimeno, J., Borge, J., Garcia-Granda, S., Novel ruthenium(II) complexes containing imino- or aminophosphine ligands for catalytic transfer hydrogenation. New J. Chem. 2003; 27: 414-420.
  • 16. Kwong, H. L., Lee, W. S., Lai, T. S., Wong, W. T., Ruthenium catalyzed asymmetric transfer hydrogenation based on chiral P,N,O Schiff base ligands and crystal structure of a ruthenium(II) complex bearing chiral P,N,O Schiff base ligands. Inorg. Chem. Com. 1999; 2: 66-69.
  • 17. Reddy, K.R., Surekha, K., Lee, G. H., Peng, S.M., Chen, J.T., Liu, S.T., Study of Insertion of Olefins and/or Carbon Monoxide into Phosphine−Imine Palladium Methyl Complexes. Organometallics, 2001; 20: 1292-1299.
  • 18. Wang, C., Friedrich, S., Youkin, T. R., Li, R. T., Grubbs, R. H., Bansleben, D. A., Day, M. W., Neutral Nickel(II)-Based Catalysts for Ethylene Polymerization. Organomet. 1998; 17: 3149-3151.
  • 19. Lavery, A., Nelson, S. M., Dinuclear intermediates in the oxidation of pendant olefinic groups of palladium(II)-co-ordinated Schiff-base ligands. J. Chem. Soc. Dalt Trans. 1984; 0: 615-620.
  • 20. Flower, K. R., Alder, M.J., Cross, W. I., Pritchard, R. G., Azo-phosphine containing complexes of Group 6 metal carbonyls: crystal and molecular structure of [Mo(CO)5{1-(4-ethylphenylazo)-6-diphenylphosphino-naphthalen-2-ol}]. J. Organomet. Chem., 1998; 568: 279-285.
  • 21. Gavrilov, K. N., Korostylev, A.V., Bondarev, O.G., Lyubimov, S. Y., Kovalevsky, A. Y., Petrovskii, P. V., Davankov, V. A., New palladium(II) complexes of (N,N-dimethylamino)alkoxy-1,3,2-oxazaphospholidine ligands. Inorg.Chim. Acta, 2000; 303: 1-6.
  • 22. Smith, G. S., Mahamo, T., Mogorosi,M. M., Moss, J. R., Mapolie, S. F., Slootweg, J.C., Lammertsma, K., Neutral palladium(II) complexes with P,N Schiff-base ligands: Synthesis, characterization and application as Suzuki–Miyaura coupling catalysts. J. Organomet.Chem. 2012; 703: 34-42.
  • 23. Andjelkovic, K., Radulovic, V., Bacchi, A., Pelizzi, G., Sladic, D., Brceski, I., Synthesis, Structure, and Antimicrobial Activity of Complexes of Pt(II), Pd(II), and Ni(II) with the Condensation Product of 2-(Diphenylphosphino)benzaldehyde and Semioxamazide. Mon. Chem.Chem. Monthly, 2006; 137: 681-691.
  • 24. Smith,G.S., Mogorosi, M. M., Mahamo, T., Moss, J. R., Mapolie, S. F., Slootweg, J. C.,Lammertsma, K., Neutral palladium(II) complexes with P,N Schiff-base ligands: Synthesis, characterization and catalytic oligomerisation of ethylene. J. Organomet. Chem. 2011; 696: 3585-3592.
  • 25. Keleş¸ M., Yılmaz, M.K., Palladium (II) complexes with aminomethylphosphine ligands as catalysts for the heck reaction. Heteroatom Chem., 2012; 23: 466-471.
  • 26. Serindağ, O., Aydın, Z., Keleş, M., Synthesis of palladium complexes with bis (diphenylphosphinomethyl) amino ligands: A catalyst for the Heck reaction of aryl halide with methyl acrylate. J. Organomet. Chem. 2007; 692: 1951-1955.
  • 27. Garrau, P.E., DELTA.R-ring contributions to phosphorus-31 NMR parameters of transition-metal-phosphorus chelate complexes. Chem. Rev. 1981; 81: 229-266.
  • 28. Smith, R.C., Bodner, C. R., Earl, M.J., Sears, N.C., Hill, N. E., Bishop, L.M., Sizemore, N.,Hehemann, D.T., Bohn, J.J., Protasiewiez, J. D., Suzuki and Heck coupling reactions mediated by palladium complexes bearing trans-spanning diphosphines. J. Organomet. Chem. 2005; 690: 477-481. DOI:
  • 29. Pramick, M. R., Rosemeier, S. M., Beranek, M. T., Nickse, S. B., Stone, J. J., Stockland, R.A., Baldwin, Kastner, S.M. M.E., Coupling of Aryl Halides with Aryl Boronic Acids with P (C6H5)(2-C6H4Cl) 2 as the Supporting Ligand. Organomet. 2003; 22: 523-528.
  • 30. Harrington, P.J., Lodewijk, E., Twenty years of naproxen technology. Org. Process Res. Dev. 1997; 1: 72-76.
  • 31. Sabounchei, S. J., Panahimehr, M., Ahmadi, M., Nasri, Z., . Khavasi, H.R., Four-coordinate Pd (II) complexes containing non-symmetric phosphorus ylides: Synthesis, characterization, and catalytic behavior towards Suzuki reaction. J. Organomet. Chem. 2013; 723: 207-213.
Year 2018, Volume: 5 Issue: 1, 133 - 148, 01.09.2017
https://doi.org/10.18596/jotcsa.341530

Abstract

References

  • 1. Aydemir, M., Baysal, A., Gümgüm, B., Synthesis and characterization of tris{2-(N,N-bis(diphenylphosphino) aminoethyl} amine derivatives: Application of a palladium(II) complex as a pre-catalyst in the Heck and Suzuki cross-coupling reactions. J. Organomet. Chem. 2008; 693: 3810-3814.
  • 2. Scrivanti, A., Beghetto, V., Matteoli, U., Antonaroli, S., Marini, A., Crociani, B., Catalytic activity of η2-(olefin)palladium(0) complexes with iminophosphine ligands in the Suzuki–Miyaura reaction. Role of the olefin in the catalyst stabilization. Tetrahedron 2005; 61: 9752-9758.
  • 3. Nadri, S., Joshaghani, M., Rafiee, E., Biphenyl-based phosphine: A well-defined, air-stable, and efficient ligand for the Mizoroki–Heck reaction. Applied Catal. A, 2009; 362: 163-168.
  • 4. Iranpoor, N., Firouzabadi, H., Motevalli, S., Talebi, M., Palladium nanoparticles supported on silicadiphenyl phosphinite (SDPP) as efficient catalyst for Mizoroki–Heck and Suzuki–Miyaura coupling reactions. J. Organomet. Chem. 2012; 708: 118-124.
  • 5. Iyer, S., Kulkarni, G.M., Ramesh, C., Mizoroki–Heck reaction, catalysis by nitrogen ligand Pd complexes and activation of aryl bromides. Tetrahedron, 2004; 60: 2163-2172.
  • 6. Gruber, A. S., Zim, D., Ebeling, G., Monteiro, A.L., Dupont, J., Sulfur-Containing Palladacycles as Catalyst Precursors for the Heck Reaction. Org. Lett. 2000; 2: 1287-1290.
  • 7. Doherty, S., Knight, J.G., Tom, H., Scanlan, T. H., Elsegood, M. R. J., Clegg,W., Iminophosphines: synthesis, formation of 2,3-dihydro-1H-benzo[1,3]azaphosphol-3-ium salts and N-(pyridin-2-yl)-2-diphenylphosphinoylaniline, coordination chemistry and applications in platinum group catalyzed Suzuki coupling reactions and hydrosilylations. J. Organomet. Chem. 2002; 650: 231-248.
  • 8. Cheng, J., Wang, F., Xu, J. H., Pan, Y., Zhang, Z., Palladium-catalyzed Suzuki–Miyaura reaction using aminophosphine as ligand. Tetrahedron Lett. 2003; 44: 7095-7098.
  • 9. Drew, D., Doyle, J. R., Cyclic diolefin complexes of platinum and palladium. Inorg. Synth. 1990; 28: 346-347.
  • 10. Laue, S., Greiner, L., Wöltinger, J., Liese, A., Continuous Application of Chemzymes in a Membrane Reactor: Asymmetric Transfer Hydrogenation of Acetophenone. Advan. Synt.& Catal. 2001; 343: 711-720.
  • 11. Keleş, M., Şahinoğlu, C., Emir, D. M., Mart, M., New iminophosphine–Ru(II) complexes and their application in hydrogenationand transfer hydrogenation. Appl. Organometal. Chem. 2014; 28: 768-772.
  • 12. Monteiro, A .L., Nobre, S. M., Pd complexes of iminophosphine ligands: A homogeneous molecular catalyst for Suzuki–Miyaura cross-coupling reactions under mild conditions. J. Mol. Catal. A 2009; 313: 65-73.
  • 13. Jeffrey, J.C., Rauchfuss, T. B., Tucker, P.A., Metal Complexes of Diiminodiphosphines. Structural and Reactivity Patterns. Inorg. Chem. 1980; 19: 3306-3315.
  • 14. Rulke, R. E., Kaasjager, V. E., Wehman, P., Elsevir, C. J., Leeuwen, P. W., Vrieze, K., Stable Palladium(0), Palladium(II), and Platinum(II) Complexes Containing a New, Multifunctional and Hemilabile Phosphino−Imino−Pyridyl Ligand:  Synthesis, Characterization, and Reactivity.Organomet. 1996; 15: 3022-3031.
  • 15. Crochet, P., Gimeno, J., Borge, J., Garcia-Granda, S., Novel ruthenium(II) complexes containing imino- or aminophosphine ligands for catalytic transfer hydrogenation. New J. Chem. 2003; 27: 414-420.
  • 16. Kwong, H. L., Lee, W. S., Lai, T. S., Wong, W. T., Ruthenium catalyzed asymmetric transfer hydrogenation based on chiral P,N,O Schiff base ligands and crystal structure of a ruthenium(II) complex bearing chiral P,N,O Schiff base ligands. Inorg. Chem. Com. 1999; 2: 66-69.
  • 17. Reddy, K.R., Surekha, K., Lee, G. H., Peng, S.M., Chen, J.T., Liu, S.T., Study of Insertion of Olefins and/or Carbon Monoxide into Phosphine−Imine Palladium Methyl Complexes. Organometallics, 2001; 20: 1292-1299.
  • 18. Wang, C., Friedrich, S., Youkin, T. R., Li, R. T., Grubbs, R. H., Bansleben, D. A., Day, M. W., Neutral Nickel(II)-Based Catalysts for Ethylene Polymerization. Organomet. 1998; 17: 3149-3151.
  • 19. Lavery, A., Nelson, S. M., Dinuclear intermediates in the oxidation of pendant olefinic groups of palladium(II)-co-ordinated Schiff-base ligands. J. Chem. Soc. Dalt Trans. 1984; 0: 615-620.
  • 20. Flower, K. R., Alder, M.J., Cross, W. I., Pritchard, R. G., Azo-phosphine containing complexes of Group 6 metal carbonyls: crystal and molecular structure of [Mo(CO)5{1-(4-ethylphenylazo)-6-diphenylphosphino-naphthalen-2-ol}]. J. Organomet. Chem., 1998; 568: 279-285.
  • 21. Gavrilov, K. N., Korostylev, A.V., Bondarev, O.G., Lyubimov, S. Y., Kovalevsky, A. Y., Petrovskii, P. V., Davankov, V. A., New palladium(II) complexes of (N,N-dimethylamino)alkoxy-1,3,2-oxazaphospholidine ligands. Inorg.Chim. Acta, 2000; 303: 1-6.
  • 22. Smith, G. S., Mahamo, T., Mogorosi,M. M., Moss, J. R., Mapolie, S. F., Slootweg, J.C., Lammertsma, K., Neutral palladium(II) complexes with P,N Schiff-base ligands: Synthesis, characterization and application as Suzuki–Miyaura coupling catalysts. J. Organomet.Chem. 2012; 703: 34-42.
  • 23. Andjelkovic, K., Radulovic, V., Bacchi, A., Pelizzi, G., Sladic, D., Brceski, I., Synthesis, Structure, and Antimicrobial Activity of Complexes of Pt(II), Pd(II), and Ni(II) with the Condensation Product of 2-(Diphenylphosphino)benzaldehyde and Semioxamazide. Mon. Chem.Chem. Monthly, 2006; 137: 681-691.
  • 24. Smith,G.S., Mogorosi, M. M., Mahamo, T., Moss, J. R., Mapolie, S. F., Slootweg, J. C.,Lammertsma, K., Neutral palladium(II) complexes with P,N Schiff-base ligands: Synthesis, characterization and catalytic oligomerisation of ethylene. J. Organomet. Chem. 2011; 696: 3585-3592.
  • 25. Keleş¸ M., Yılmaz, M.K., Palladium (II) complexes with aminomethylphosphine ligands as catalysts for the heck reaction. Heteroatom Chem., 2012; 23: 466-471.
  • 26. Serindağ, O., Aydın, Z., Keleş, M., Synthesis of palladium complexes with bis (diphenylphosphinomethyl) amino ligands: A catalyst for the Heck reaction of aryl halide with methyl acrylate. J. Organomet. Chem. 2007; 692: 1951-1955.
  • 27. Garrau, P.E., DELTA.R-ring contributions to phosphorus-31 NMR parameters of transition-metal-phosphorus chelate complexes. Chem. Rev. 1981; 81: 229-266.
  • 28. Smith, R.C., Bodner, C. R., Earl, M.J., Sears, N.C., Hill, N. E., Bishop, L.M., Sizemore, N.,Hehemann, D.T., Bohn, J.J., Protasiewiez, J. D., Suzuki and Heck coupling reactions mediated by palladium complexes bearing trans-spanning diphosphines. J. Organomet. Chem. 2005; 690: 477-481. DOI:
  • 29. Pramick, M. R., Rosemeier, S. M., Beranek, M. T., Nickse, S. B., Stone, J. J., Stockland, R.A., Baldwin, Kastner, S.M. M.E., Coupling of Aryl Halides with Aryl Boronic Acids with P (C6H5)(2-C6H4Cl) 2 as the Supporting Ligand. Organomet. 2003; 22: 523-528.
  • 30. Harrington, P.J., Lodewijk, E., Twenty years of naproxen technology. Org. Process Res. Dev. 1997; 1: 72-76.
  • 31. Sabounchei, S. J., Panahimehr, M., Ahmadi, M., Nasri, Z., . Khavasi, H.R., Four-coordinate Pd (II) complexes containing non-symmetric phosphorus ylides: Synthesis, characterization, and catalytic behavior towards Suzuki reaction. J. Organomet. Chem. 2013; 723: 207-213.
There are 31 citations in total.

Details

Subjects Engineering, Chemical Engineering
Journal Section Articles
Authors

Mustafa Kemal Yılmaz 0000-0002-9969-3956

Mustafa Keleş 0000-0003-2669-1818

Publication Date September 1, 2017
Submission Date October 3, 2017
Acceptance Date January 2, 2018
Published in Issue Year 2018 Volume: 5 Issue: 1

Cite

Vancouver Yılmaz MK, Keleş M. The catalytic activity of Palladium(II) complexes containing PN ligands in the Heck and Suzuki C-C coupling reactions. JOTCSA. 2017;5(1):133-48.